Sodium Hydroxide → 5,5-Dimethyl-5,6-dihydro-8-(2-thienyl)-naphthalene-2-carboxylic acid

HRID 2085861Notes

Reaction equation

[CH3:1][C:2]1([CH3:21])[CH2:11][CH:10]=[C:9]([C:12]2[S:13][CH:14]=[CH:15][CH:16]=2)[C:8]2[CH:7]=[C:6]([C:17]([O:19]C)=[O:18])[CH:5]=[CH:4][C:3]1=2.[OH-].[Na+]>CCO.C1COCC1>[CH3:1][C:2]1([CH3:21])[CH2:11][CH:10]=[C:9]([C:12]2[S:13][CH:14]=[CH:15][CH:16]=2)[C:8]2[CH:7]=[C:6]([C:17]([OH:19])=[O:18])[CH:5]=[CH:4][C:3]1=2

Participants

Conditions

Temperature: 35 °C

Procedure

To a solution of methyl 5,5-dimethyl-5,6-dihydro-8-(2thienyl)-2-naphthalenecarboxylate (Compound E5, 430.0 mg, 1.44 mmol) in 3.0 mL of EtOH and 3.0 mL THF was added NaOH (240.0 mg, 6.00 mmol; 3.0 mL of a 2N aqueous solution). The resulting solution was warmed to 35° C. for 6 h, cooled to room temperature and quenched with 1M HCl. The mixture was extracted with EtOAc and the combined organic layers washed with H2O and saturated aqueous NaCl before being dried over MgSO4. Removal of the solvents under reduced pressure afforded the title compound as a pale yellow solid.

Workup

temperaturecooled to room temperature
customquenched with 1M HCl
extractionThe mixture was extracted with EtOAc
washthe combined organic layers washed with H2O and saturated aqueous NaCl
dry with materialbefore being dried over MgSO4
customRemoval of the solvents under reduced pressure

Sources & evidence

ORD record: ord-339b6a20fa0c4fdcac5312fadf467a59
Source dataset: uspto-grants-2004_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06720425B2

Reaction notes

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